Skip to main content
. Author manuscript; available in PMC: 2013 Apr 16.
Published in final edited form as: Angew Chem Int Ed Engl. 2012 Mar 5;51(16):3923–3927. doi: 10.1002/anie.201109044

Table 3.

Scope of pyrrolidine synthesis.[a]

Entry Substrate Product Yield [%][b] ee [%][c]
graphic file with name nihms362194t1.jpg graphic file with name nihms362194t2.jpg
1 7a, R1 =Me, R2 =Ts 8a 81 88
2 7b, R1 =Me, R2 =Ms 8b 78 43
3 7c, R1 =Me, R2 =Ns 8c 80 60
4 7d, R1 =Ph, R2 =Ts 8d 85 93
5 7e, R1 =H, R2 =Ts 8e 77 73
6 7f, R1 =H, R2 =3,5-di-tBu-C6H3SO2 8f 85 88
7 graphic file with name nihms362194t3.jpg
7g
graphic file with name nihms362194t4.jpg
8g
78 92
8 graphic file with name nihms362194t5.jpg
9
graphic file with name nihms362194t6.jpg
10
78 83
9 graphic file with name nihms362194t7.jpg
11
graphic file with name nihms362194t8.jpg
12
74 16
10[d] graphic file with name nihms362194t9.jpg
13
graphic file with name nihms362194t10.jpg
14
73 27
[a]

Reactions run as described in Table 1, entry 7 except reaction time was extended to 11h.

[b]

Yield of product isolated by flash chromatography on SiO2.

[c]

Enantioselectivity determined by HPLC on a chiral stationary phase.

[d]

Ligand 2 was used.